羰基催化大环化合成平面手性吲哚。

IF 16.1 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Dr. Gongming Yang, Yi He, Tianyi Wang, Zhipeng Li, Prof. Dr. Jian Wang
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引用次数: 0

摘要

吲哚基平面手性大环广泛存在于天然产物和生物活性分子中。然而,与吲哚基轴向手性结构的制备形成鲜明对比的是,吲哚基平面手性大环的对映选择性催化至今仍是一项艰巨的任务。本文报道了一种n -杂环羰基(NHC)催化的3-甲醛吲哚/吡咯分子内逆选择性大环化反应,该反应具有底物范围广和良好的官能团耐受性,可以快速获得多种基于吲哚/吡咯的平面手性大环,具有各种环大小(10-16个成员),产率高,对映选择性好。重要的是,通过该方法可以直接有效地获得具有平面手性和轴向手性的吲哚基大环结构,具有良好的对映选择性和非对映选择性。此外,这些合成的平面手性大环为化学家开发新的催化剂或配体以及新的反应提供了许多可能性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Atroposelective Synthesis of Planar-Chiral Indoles via Carbene Catalyzed Macrocyclization

Atroposelective Synthesis of Planar-Chiral Indoles via Carbene Catalyzed Macrocyclization

Indole-based planar-chiral macrocycles are widely found in natural products and bioactive molecules. However, in sharp contrast to the preparation of indole-based axially chiral structures, the enantioselective catalysis of indole-based planar-chiral macrocycles is still a formidable task so far. Here we report an N-heterocyclic carbene (NHC)-catalyzed intramolecular atroposelective macrocyclization of 3-carboxaldehyde indole/pyrroles, featuring with broad substrate scope and good functional group tolerance, and allowing for a rapid access to diverse indole/pyrrole-based planar-chiral macrocycles with various tether-lengths (10–16 members) in good yields and with excellent enantioselectivities. Importantly, the indole-based macrocyclic structures with both planar and axial chirality were directly and efficiently obtained through this protocol with excellent enantioselectivities and diastereoselectivities. In addition, these synthesized planar-chiral macrocycles offer many possibilities for chemists to develop new catalysts or ligands, as well as new reactions.

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来源期刊
CiteScore
26.60
自引率
6.60%
发文量
3549
审稿时长
1.5 months
期刊介绍: Angewandte Chemie, a journal of the German Chemical Society (GDCh), maintains a leading position among scholarly journals in general chemistry with an impressive Impact Factor of 16.6 (2022 Journal Citation Reports, Clarivate, 2023). Published weekly in a reader-friendly format, it features new articles almost every day. Established in 1887, Angewandte Chemie is a prominent chemistry journal, offering a dynamic blend of Review-type articles, Highlights, Communications, and Research Articles on a weekly basis, making it unique in the field.
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